Potassium Carbonate → HCID 59803681, compound

HRID 1666217Notes

Reaction equation

HRID 1666217 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]#[C:12][C:13]2[N:21]([CH3:22])[C:20]3[C:19](=[O:23])[N:18]([CH2:24][C:25]#[CH:26])[C:17](=[O:27])[NH:16][C:15]=3[N:14]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].COC1C=C(C#CC2N(C)C3C(=O)N(CC#C)C(=O)N(C)C=3N=2)C=CC=1OC.C(=O)([O-])[O-].[K+].[K+].[C:62]([O:68][CH2:69]Cl)(=[O:67])[C:63]([CH3:66])([CH3:65])[CH3:64]>CN(C=O)C>[C:62]([O:68][CH2:69][N:16]1[C:15]2[N:14]=[C:13]([C:12]#[C:11][C:5]3[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=3)[N:21]([CH3:22])[C:20]=2[C:19](=[O:23])[N:18]([CH2:24][C:25]#[CH:26])[C:17]1=[O:27])(=[O:67])[C:63]([CH3:66])([CH3:65])[CH3:64]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 87885Chloromethyl pivalateHCID 25062694HCID 25062694, compoundHCID 59803663HCID 59803663, compound

Product 1

HCID 59803681HCID 59803681, compoundYield 79.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The crude 8-[(3,4-dimethoxyphenyl)ethynyl]-7-methyl-1-prop-2-ynyl-3,7-dihydro-1H-purine-2,6-dione (ca. 452 mg, 1.24 mmol), contaminated with the starting material and with the dimethylated derivative (8-[(3,4-dimethoxyphenyl)ethynyl]-3,7-dimethyl-1-prop-2-ynyl-3,7-dihydro-1H-purine-2,6-dione), was suspended in dry DMF (7 mL). Subsequently dry potassium carbonate (514 mg, 3.72 mmol) and chloromethyl pivalate (654 mg, 4.34 mmol) was added. The mixture was stirred at room temperature for 3 h (TLC-control: dichloromethane/methanol, 9.5:0.5, Rf=0.60 for the main product) and the product was precipitated by adding water (30 mL), filtered under reduced pressure and dried at 70° C. The crude product was dissolved in a minimum of ethyl acetate (by slightly heating) and purified by column chromatography (eluent: petroleum ether/ethyl acetate, 1:1) affording 471 mg (79% yield over two steps) of {8-[(3,4-dimethoxyphenyl)ethynyl]-7-methyl-2,6-dioxo-1-prop-2-ynyl-1,2,6,7-tetrahydro-3H-purin-3-yl}methyl pivalate as a colorless solid.

Workup

  1. customdichloromethane/methanol, 9.5:0.5, Rf=0.60 for the main product) and the product was precipitated
  2. additionby adding water (30 mL)
  3. filtrationfiltered under reduced pressure
  4. customdried at 70° C
  5. dissolutionThe crude product was dissolved in a minimum of ethyl acetate (
  6. temperatureby slightly heating) and
  7. custompurified by column chromatography (eluent: petroleum ether/ethyl acetate, 1:1)

Sources & evidence

ORD record
ord-a8f6d115688843aaab62edee3dfadfe7
Source dataset
uspto-grants-2011_10
Patent number
US08044061B2

Reaction notes

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